Iridium-Catalyzed Asymmetric Hydrogenation of α-Alkylidene Succinimides

被引:102
作者
Liu, Yuanyuan [1 ]
Zhang, Wanbin [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; hydrogenation; iridium; ligand effects; synthetic methods; HIGHLY ENANTIOSELECTIVE HYDROGENATION; SPIRO AMINOPHOSPHINE LIGANDS; DIELS-ALDER REACTIONS; OXAZOLINE LIGANDS; 1,3-DIPOLAR CYCLOADDITIONS; ALLYLIC ALKYLATION; CARBONYL-COMPOUNDS; C(SP(3))-H BONDS; CHIRAL SWITCH; COMPLEXES;
D O I
10.1002/anie.201209126
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Not to be out PhOXed! The title reaction provides a new approach to chiral succinimide derivatives with excellent yields and ee values by using a low catalyst loading (0.05 mol %) and mild reaction conditions. Chiral 3-benzyl pyrrolidines and 1-hydroxypyrrolidine-2,5-diones, important structural motifs in natural products and pharmaceuticals, could be readily prepared. BARF -=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2203 / 2206
页数:4
相关论文
共 50 条
  • [21] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Exocyclic C=C Bonds
    Xia, Jingzhao
    Yang, Guoqiang
    Zhuge, Ruijing
    Liu, Yangang
    Zhang, Wanbin
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (51) : 18354 - 18357
  • [22] Enantioselective Synthesis of Chiral Tetrahydroisoquinolines by Iridium-Catalyzed Asymmetric Hydrogenation of Enamines
    Yan, Pu-Cha
    Xie, Jian-Hua
    Hou, Guo-Hua
    Wang, Li-Xin
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3243 - 3250
  • [23] Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Piperazin-2-ones
    Wang, Yanzhao
    Liu, Yuanyuan
    Li, Kun
    Yang, Guoqiang
    Zhang, Wanbin
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (11) : 1933 - 1941
  • [24] Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Enamines
    Hou, Guo-Hua
    Xie, Jian-Hua
    Yan, Pu-Cha
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (04) : 1366 - +
  • [25] Progress in Iridium-Catalyzed Asymmetric Hydrogenation Reactions
    Zhang, Junfang
    Yang, Dingqiao
    Long, Yuhua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (06) : 835 - 847
  • [26] Highly Selective Iridium-Catalyzed Asymmetric Hydrogenation of Trifluoromethyl Olefins: A New Route to Trifluoromethyl-Bearing Stereocenters
    Engman, Mattias
    Cheruku, Pradeep
    Tolstoy, Paivi
    Bergquist, Jonas
    Volker, Sebastian F.
    Andersson, Pher G.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) : 375 - 378
  • [27] A mechanistic investigation of an Iridium-catalyzed asymmetric hydrogenation of pyridinium salts
    Huang, Yuhua
    Liu, Shaodong
    Liu, Yizhou
    Chen, Yonggang
    Weisel, Mark
    Williamson, R. Thomas
    Davies, Ian W.
    Zhang, Xumu
    TETRAHEDRON, 2018, 74 (17) : 2182 - 2190
  • [28] Highly Enantioselective Iridium-Catalyzed Hydrogenation of α,β-Unsaturated Esters
    Li, Jia-Qi
    Quan, Xu
    Andersson, Pher G.
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (34) : 10609 - 10616
  • [29] Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of -Alkyl--Ketoesters
    Bao, Deng-Hui
    Wu, Hui-Ling
    Liu, Chao-Lun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8791 - 8794
  • [30] Iridium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted Nitroalkenes
    Liu, Man
    Kong, Duanyang
    Li, Meina
    Zi, Guofu
    Hou, Guohua
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) : 3875 - 3879